Fijlip kacer



} philosophy and chemist, su-b'ect of the King and sulfuryl chlorid) onanacetylated amido- 0 a diacetyl amido-anthraq'u-inone compound, or anacetylated d1amido-anthraqumone of these compounds can be employed. In-

pend upon the acetylamido anthraquinone shouldpreferably be dye whileusing less which respectively dye cotton orange-red aniido-anthra uinonecom ound with phos- Processes of Making the Same, of which the followingis a specification.

UNITED STATES PATENT OFFICE.

FILIP KACEKOF MANNHEIM, GERMANY, ASSlGNOlt TO BADISCl-IE ANILlN & SODAFABRlK,

OF LUDWIGSHAFEN-ON PBERHINE, GERMANY, A CORPORATION.

COMPOUND. 01 THE ANTHRACENE SERIES AND PROCESS OF MAKING SAME.

Specification of Letters Patent.

Patented. June 22, 1909.

Application filed March 2, '19Q8. Serial No. 418,850.

T 0 all whom it may concern:

.Be'it known that I, FILIP KAeER, doctor of oi Prussia, residing at Manneim, Germany, have lnvented new and useful Improvements in Compounds ofthe Anthracen-e Series and I have discovered that by reacting with anacid chlorid (such for instance as phosphorus oxyehlorid, phosphoruspenta-chlorid anthra-qum-one compound I can obtain valuable condensationproducts. For the purposes of 'my invention either a monoacetyl orcompound, or a mixture of any two, or more,

stead of any one, or more, of the above mentloned .compounds, its, ortheir, halogen derivative, or derivatives, can be employed.- The resultsobtalned during the reaction decompound, employed. Most of them dyecotton from the vat shades which vary in color and intensity. Theroducts obtained caustic soda and a lower temperature than usual andalso with the addition of some Glaubers salt to the vat, l-acetylamidoamixture of 1-acetylamido-anthraquinone with 2--acetylamido-anthra uinonea yellow vat dyestutl is obtained. y reacting with phosphorus oxychloridon the acetyl comound of the diamidoanthraquinone obtainable by reducingthe easily soluble alphadinitro-anthraqumone described in thespecification of German Patent No. 72,685 abrown' vat dyestufi isobtained, but by employing a mixture of this acetyl compound wlth 1-acet l-amid0 anthraquinone, or with 2-acetylami anthraquinone, productsare obtained and yellow shades. The acetylation f of theamido-anthrauinone compound and the treatment with t e acid chlorid canbe made to take place in one operation; for instance, by heating thephorus oxych orid, or osphorus pentachlorid, andacetic an ydrid, .oracetyl chlorid, or sodium acetate, the new condensation products aredireptly obtained. If sulfuryl chlorid be employed as the acid chlorid,chlorination of the anthraquinone residue can also be efiected in oneoperation. 7"

The compounds obtained according to my invention possess weak basicproperties and have a light brown to red color. They are insoluble inwater and in dilute acids and alkalies, and are, difiicultly soluble inmost organic solvents. In sulfuric acid they yield red solutions. Theydiffer from the acetylamid-o anthraquinone compounds irom which theyhave been prepared in that they are not reconverted into theamido-anthra quinone compounds on treating them with saponifying agents,such for instance as sulfuric acid at a temperature of from 70 to 80 C,Most of the com ounds are themselves coloring matters an some can beused for the preparation of coloring matters.

The following examples will serve to illustrate further the nature of myinvention and how it can be carried into practical effect, but

the invention is not confined to these examples. The parts are byweight.

Example 1: Boil together in a reflux apparatus one (1) part ofl-acetyl-amido-anthraquinone and two (2) arts of phosphorus oxychloniduntil the so ution which is at first forl'nedis converted into a yellowcr'ystalline mass. Then. dissolve the melt in from eight (8'), to ten(10), parts of concentrated sulfuric acid and allow the clear redsolution to run slowly, while stirring, into one hundred (100) arts ofwater and then filter ofi, wash and dry the preci itate, which 1s thenin the condition of a re. powder.

Example 2: Boil together, for about ten (10) minutes, in a refluxapparatus, one (1) part of 2-acetyl-amido-anthraquinone and two (2)parts of phos horus oxychlorid and work up as describe in the foregoingExample 1. The product is a light brown powder which, in sulfuric acid,yields a red solution with a violet tinge.

Example 3: Boil together, for about ten (10),'minutes, in a refluxapparatus, one (1) art of 1eacetylamido-anthraquinone, one (1) art of2-acetyl-amido-anthraquinone and our (4) parts of phosphorus oxyehlorid.The productobtained is, when dry, a light brown p wder which yields ared solution in sulfuric acid.

Example 4: Boil to ether,-for about ten (10) minutes, in a re uxapparatus, three acetylating the alphainitro-anthraquinone described inthe specification of German Patcut 7 2 ,685). The product obtained is a.redbrown powder which yields a red solution in sulfuric acid and dyescotton, from a hydro.- sulfite vat, orarli ge-red shades.

Example 5: eat together, for about three .(3) hours, at a temperature offrom seventy (70), to eighty (80), degrees centigrade, one

' hundred (100) parts of 2.4-dibrom-l-amidoanthraquinone, one hundred(100) parts of phosphorus oxychlorid and thirteen and a alf (13.5) partsof acetic anhydrid, and then' work up as described in the foregoing Ex-'ample 1. The product obtained is a brown powder.

Example 6: Warm together gently, for about one (1) hour, in a re uxapparatus, one (1) part of l -amido-anthraquinone and four (4) parts ofsulfuryl chlorid. A homogeneous crystalline magmafcontaining an excessof sulfuryl chlorid. is thus obtained. Then add one (1) part of aceticanhydrid and heat until solution is effected. On working up the productas described in the foregoing Examp e 1, a yellow-brown powder isobtained.

Now what I claim is: I

1. The process of producing compounds of the anthracene series byreacting with an acid chlorid on an acetylated amidoanthraquinonecompound.

2. The process of producing compounds of the anthracene series byreacting with an acid chlorid on a mixture of a plurality of vacetylatedamidoanthraquinone compounds.

3. The process of producing compounds of the anthracene series byreacting on an ture of a plurality of amidoanthraquinonecompounds withan acid chlorid and with an acetylating agent.

5. As new artlcles of manufacture the com ounds ,of the anthraceneseries which can e obtained -by reacting with an acid chlorid on anacetylated amidoanthraquinone compound, which new compounds pos-g sessweak basic properties and have a light brown to red color, are insolublein water and in dilute acids and alkalies and are diflicultly soluble inmost organic solvents, but yield red solutions in "concentrated sulfuricacid and remain unaltered on being heated with sulfuric acid at atemperature of 70 C.

6. As a new article of manufacture the coling matter of the anthraceneseries which can be obtained by reacting with phosphorus oxychlorid on amixture of 1-acetylamidoanthraquinone and diacetyldiamidoanthraquinonewhich coloring matter possesses Weak basic properties and in the form.of powder possesses a red-brown color and is insoluble in water and indilute acids and alkalies and is difficultly soluble in most organicsolvents but yields a red solution in concentrated sulfuric acid andremains unaltered'on being heated with sulfuric acid at a temperature of7 0 C. and which dyes cotton'from a hydrosulfite vat orangered shades.

In testimony whereof I have hereunto set myhand in the presence of twosubscribing witnesses.

FILIP

